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Uptown’s Wilson Winter Walk Turns Into DIY Event With Cash Prizes For Shopping Local

Wilson Avenue will still be decked out in holiday decorations, but no in-person events will take place.

Uptown's giant advent calendar on display at 935 W. Wilson Ave.
Facebook/Wilson Abbey Windows
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UPTOWN — Uptown business leaders are pandemic-proofing their holiday events and promotions — and offering cash prizes for shopping local.

This would have been the seventh year of the Winter Walk on Wilson, where businesses along the Wilson Avenue commercial corridor host events, give away items and provide holiday entertainment.

But because of the coronavirus pandemic, the local chamber will host Winter Warmth in Uptown, a campaign to put neighbors in the holiday spirit and reward local shopping.

Starting Friday, Wilson Avenue will be decorated with holiday colors. Motivational messages will also pop up along the street, according to Uptown United, the community development group organizing the event.

New this year will be a prizes for shopping locally, with over $650 in award money being given out.

A $100 prize will be given each week through the end of December, with a $250 grand prize awarded at the end of the month.

Each week in December will have a theme, and neighbors who buy a local good corresponding to that theme can be entered into the prize giveaway.

The themed weeks:

  • Dec. 4-10: Warm Up Wilson. Buy a good from a business on Wilson Avenue in Uptown to be qualified for that week’s prize.
  • Dec. 11-17: Warm Your Wallet. Any purchase from a local Uptown business can be used to enter the weekly giveaway.
  • Dec. 18-24: Warm Your Heart. Donate time, money or a gift to a local organization or non-profit to be included in the weekly giveaway. For some ideas on local charitable giving, click here.
  • Dec. 25-31: Warm Your Belly. Buy a food or drink item from an Uptown establishment to be entered into the giveaway.

Neighbors can submit entries to the contest by sharing a photo of the purchase while tagging the business and @exploreuptownchi on Instagram or @uptownchamber on Facebook with the hashtag #winterwarmthuptown.

Emailing receipts of local purchases to with the subject line #winterwarmthuptown will also count as entries to the weekly prize giveaways. Each receipt counts as one entry.

People who participate in each of the themed weeks will be entered into the grand prize giveaway, which is $250 in gift cards to local businesses.

For more information on the event, click here.

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